CN105377935B - Nonfluorinated carbamate base coating - Google Patents
Nonfluorinated carbamate base coating Download PDFInfo
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- CN105377935B CN105377935B CN201480030559.7A CN201480030559A CN105377935B CN 105377935 B CN105377935 B CN 105377935B CN 201480030559 A CN201480030559 A CN 201480030559A CN 105377935 B CN105377935 B CN 105377935B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/568—Reaction products of isocyanates with polyethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/572—Reaction products of isocyanates with polyesters or polyesteramides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2164—Coating or impregnation specified as water repellent
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a kind of for assigning base material water-resistance and the compound of optional soil release performance, wherein the compound is prepared by following steps：(i) so that (a) is selected from compound of at least one of isocyanates, diisocyanate, polyisocyanates or their mixture containing isocyanate groups, and (b) be selected from least one isocyanate-reactive compound reaction of formula (Ia), (Ib) or (Ic)：
Description
Technical field
The present invention relates to include the organic amino first that can be used for assigning the durable water-resistance and optional soil release performance of textile fabric
The composition of ester compound, the compound are derived from isocyanates and biology base organic compound such as D-sorbite, lemon
Acid esters and pentaerythrite.
Background technology
Known numerous compositions are used as inorganic agent to provide water-resistance and optional soil release performance to textile substrates.It is many this
Class inorganic agent is fluorinated polymer and copolymer or nonfluorinated polymers and copolymer.Non-fluorinated compound is mainly polypropylene
Perester radical or carbamate base co-polymer.
Fluorinated copolymers provide good water-resistance and grease resistance.Various trials have been carried out to generate nonfluorinated water resistant
Agent.Known nonfluorinated copolymer provides water-resistance and optional soil release performance to textile fabric, but its validity is corresponded to less than fluorination
Object.
Moore discloses the polyether polyols for providing moisture-proof in United States Patent (USP) No.6,864,312.Moore requirements
Protection to polyether polyols particle dispersion, wherein polyether polyols are the systems by including polyisocyanates and polyalcohol
Isocyanate-terminated prepolymer prepared by agent.
Invention content
Such Non-fluorinated compound is needed, which provides water-resistance and optional decontamination for textile fabric
Property, have and the comparable results of property of fluorination treatment agent.It is also contemplated that can be Non-fluorinated compound derived from biology base.This hair
It is bright to meet these demands.
The present invention includes the organic amino of nonfluorinated that can be used for assigning the durable water-resistance and optional soil release performance of textile fabric
Formic acid ester compound, copolymer are derived from the organic D-sorbite of biology base and isocyanates.These nonfluorinated carbamates to
Textile fabric provides increased durable water-resistance and optional soil release performance, and can be with several fluorination water resistant immunomodulator compounds phases
Than.
The present invention includes the compound for assigning base material water-resistance and optional soil release performance, wherein the compound passes through
It is prepared by the process included the following steps：
(i) (a) is made to be selected from least one of isocyanates, diisocyanate, polyisocyanates or their mixture
Compound containing isocyanate groups, and (b) it is selected from formula (Ia), (Ib) or at least one of (Ic) or their mixture
Isocyanate-reactive compound reacts：
Wherein each R independently is-H；-R1；-C(O)R1；-(CH2CH2O)n(CH(CH3)CH2O)mR2；Or-(CH2CH2O)n
(CH(CH3)CH2O)mC(O)R1；
Each n is independently 0 to 20；
Each m is independently 0 to 20；
M+n is more than 0；
Each R1It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base group；
Each R2It independently is-H or includes with 6 to 30 carbon and optionally the straight chain or branch of at least one unsaturated bond
Chain alkylene group；
Precondition is the then R or R when compound has formula (Ia)2At least one of be-H；
Each R3It independently is-H；-R1；-C(O)R1；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’
(CH(CH3)CH2O)m’C(O)R1；
Each R4It independently is-H, includes with 6 to 30 carbon and optionally the linear chain or branched chain of at least one unsaturated bond
Hydrocarbyl group or combination thereof；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C
(O)R1；
Each n ' is independently 0 to 20；
Each m ' is independently 0 to 20；
M '+n ' is more than 0；
Precondition is then at least one R when compound is formula (Ib)2、R3Or R4For-H；And
Each R19For-H ,-C (O) R1Or-CH2C[CH2OR]3,
Precondition is then at least one R when compound is formula (Ic)19Or R is-H.
Compound also may include other reactant, such as the second organic compound and/or water.Water can be used for making unreacted
It is isocyanate-crosslinked to generate urea bond.
In a second embodiment, the present invention is the method for preparing composition, and this method includes：(i) (a) is made to be selected from isocyanic acid
Compound of at least one of ester, diisocyanate, polyisocyanates or their mixture containing isocyanate groups, and
(b) at least one isocyanate-reactive compound for being selected from formula (Ia), (Ib) or (Ic) reacts.
In the third embodiment, the present invention is the method for the treatment of of fibrous substrates, and this method includes applying to the surface of base material
Nonfluorinated silylorganocarbamate as described above.
In the fourth embodiment, the present invention is with the compound or composition as described above being applied on its surface
Fiber base material.
In the 5th embodiment, the present invention is the composition for assigning base material water-resistance and optional soil release performance, the group
Close aqueous solution or dispersion that object includes at least one nonfluorinated silylorganocarbamate compound as described above.
Specific implementation mode
Herein, all trade marks are marked with capitalization.
The present invention provides the compounds for assigning fiber base material water-resistance and optional soil release performance.It can quotient with traditional
Purchase obtain nonfluorinated inorganic agent compare, gained compound to the base material of processing provide enhancing performance and water-resistance it is durable
Property.The starting material of the present invention can be derived from biological source material.
The present invention includes the compound for assigning base material water-resistance and optional soil release performance, wherein the compound passes through
It is prepared by the process included the following steps：
(i) (a) is made to be selected from least one of isocyanates, diisocyanate, polyisocyanates or their mixture
Compound containing isocyanate groups, and (b) it is selected from formula (Ia), (Ib) or at least one of (Ic) or their mixture
Isocyanate-reactive compound reacts：
Wherein each R independently is-H；-R1；-C(O)R1；-(CH2CH2O)n(CH(CH3)CH2O)mR2Or-(CH2CH2O)n
(CH(CH3)CH2O)mC(O)R1；
Each n is independently 0 to 20；
Each m is independently 0 to 20；
M+n is more than 0；
Each R1It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base group；
Each R2It independently is-H or includes with 6 to 30 carbon and optionally the straight chain or branch of at least one unsaturated bond
Chain alkylene group；
Precondition is the then R or R when compound has formula (Ia)2At least one of be-H；
Each R3It independently is-H；-R1；-C(O)R1；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’
(CH(CH3)CH2O)m’C(O)R1；
Each R4It independently is-H, includes with 6 to 30 carbon and optionally the linear chain or branched chain of at least one unsaturated bond
Hydrocarbyl group or combination thereof；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C
(O)R1；
Each n ' is independently 0 to 20；
Each m ' is independently 0 to 20；
M '+n ' is more than 0；
Precondition is then at least one R when compound is formula (Ib)2、R3Or R4For-H；And
Each R19For-H ,-C (O) R1Or-CH2C[CH2OR]3,
Precondition is then at least one R when compound is formula (Ic)19Or R is-H.
For formula (Ia), the compound of (Ib) or (Ic) ,-(CH2CH2O)-expression ethylene oxide group (EO), and-(CH
(CH3)CH2O)-indicate oxypropylene group (PO).These compounds may include only EO groups, only PO groups or their mixing
Object.For example, these compounds are alternatively arranged as being expressed as the three-of PEG-PPG-PEG (polyethylene glycol propylene glycol-polyethylene glycol)
Block copolymer exists.
In one embodiment, for assign the compound of base material water-resistance and optional soil release performance by following steps come
It prepares：(i) isocyanates that keeps (a) at least one containing isocyanate groups, diisocyanate, polyisocyanates or theirs is mixed
Close the compound reaction of object and formula (Ia).Wherein at least one of R is-H and at least one R is selected from-C (O) R1Formula
(Ia) compound is commonly known as alkyl D-sorbite.- C (O) R can be used in these D-sorbites1Monosubstituted, two substitutions three take
Generation.It is known that commercially available D-sorbite, such as SPAN, scope from wherein each R be H (unsubstituted) to its
In each R be-C (O) R1The mixture of the various D-sorbites of the D-sorbite of (substitution completely), wherein R1To have 5 to 29
The linear chain or branched chain hydrocarbyl group of carbon；And the mixture of their various substituent groups.Commercially available D-sorbite may be used also
Including a certain amount of sorbierite, isobide or other intermediates or by-product.
In a preferred embodiment, at least one R is-C (O) R1, and R1To have 5 to 29 carbon, more preferably 7
To 21 carbon, and the most preferably straight chain branched chain hydrocarbyl groups of 11 to 21 carbon.Preferred compound include derived from octanoic acid,
Capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid and their mixing
The monosubstituted of object, two substitutions and three substitution D-sorbites.Particularly preferred compound include it is monosubstituted, two substitution and it is trisubstituted
Sorbitan stearate or D-sorbite docosane acid esters.
Optionally, R1For with 5 to 29 carbon and include at least one unsaturated bond linear chain or branched chain hydrocarbyl group.Its
In at least one R be selected from-C (O) R1, and R1Including the example of the compound of the formula (Ia) of at least one unsaturated bond includes but not
It is limited to D-sorbite trioleate (that is, wherein R1For-C7H14CH=CHC8H17).Other examples include but not limited to derived from palm fibre
Palmitic acid oleic acid, linoleic acid, arachidonic acid and the monosubstituted of erucic acid, two substitutions and three substitution D-sorbites.
In one embodiment, using the compound of formula (Ia), wherein at least one R independently is-(CH2CH2O)n(CH
(CH3)CH2O)mR2Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1.Wherein at least one R is-(CH2CH2O)n(CH(CH3)
CH2O)mR2Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, wherein each m is independently 0 to 20, each n independently is 0
To 20, and the compound of formulas (Ia) of the n+m more than 0 is referred to as polysorbate and can be to be obtained commercially available from trade name TWEEN
.These polysorbate can use hydrocarbyl group R1Or R2Monosubstituted, two substitutions or three substitutions.It is known that commercially available
Polysorbate scope is from wherein each R2Wherein each R is arrived for H is (unsubstituted)1For with 5 to 29 carbon straight chain or
The mixture of the various polysorbate of the polysorbate of branched chain hydrocarbyl groups (substitution completely)；And their various substitutions
The mixture of object.The example of the compound of formula (Ia) includes polysorbate, such as three stearic acid polysorbate and single tristearin
Sour polysorbate.Wherein m+n is more than 0, and wherein R1Include the example of the compound of the formula (Ia) of at least one unsaturated bond
It is not limited to three oleic acid polysorbate (wherein R1For C7H14CH=CHC8H17) and it is commercially available with title polysorbate80.Reagent
It may include having and be directed to R, R1And R2Various values compound mixture, and also may include wherein R1Including at least one
The compound of unsaturated bond and wherein R1The mixture of fully saturated compound.
The compound of formula (Ib) is referred to as alkyl citrate.These citrates may be present to be taken with hydrocarbyl group list
Generation, two substitutions or three substitutions.It is known that commercially available citrate includes various citrates and from wherein R3With
Each R4For the citric acid of-H, wherein each R is arrived4It is with 6 to 30 carbon and optionally straight comprising at least one unsaturated bond
The mixture of the citrate of chain or branched chain hydrocarbyl groups；And the mixture of their various substituent groups.Can be used has needle
To R1、R2、R3And R4Various values citrate mixture, and it also may include wherein R1Including at least one unsaturation
The compound of key and wherein R1The mixture of fully saturated compound.Also commercially available (wherein the m '+n ' of alkyl citrate
More than 0, R4For-(CH2CH2O)n’(CH(CH3)CH2O)m’R2Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1), and deposit
It is from wherein R3With each R2For H to wherein each R1And/or R2For have 5 to 30 carbon and optionally include at least one not
In the various substituent groups of the linear chain or branched chain hydrocarbyl group of saturated bond.The example of the compound of formula (Ib) includes but not limited to three hydrocarbon
Base citrate.
The compound of formula (Ic) is referred to as pentaerythritol ester.These pentaerythritol esters may be present to be taken with hydrocarbyl group list
Generation, two substitutions or three substitutions.The compound of preferred formula (Ic) is dipentaerythritol ester, wherein R19For-CH2C[CH2OR]3.
Know, commercially available pentaerythritol ester includes wherein R19With the various pentaerythritol esters that each R is-H, arrive wherein each
R is-C (O) R1And R1To include with 5 to 29 carbon and optionally the linear chain or branched chain hydrocarbyl group of at least one unsaturated bond
Pentaerythritol ester mixture；And the mixture of their various substituent groups.Pentaerythritol ester, which also may include having, is directed to R
Different chain length mixture or in which R1Including the compound of at least one unsaturated bond and wherein R1Fully saturated chemical combination
The compound of the mixture of object.
The compound of formula (Ia), (Ib) and (Ic) can be derived from all biology bases.It is so-called to mean " derived from biology base "
At least 10% material can be by non-crude petroleum sources, and such as plant, other vegetation and tallow manufacture.In one embodiment, formula
(Ia), the compound of (Ib) and (Ic) are about 10% to 100% biology base.In one embodiment, formula (Ia), (Ib) and
(Ic) compound is about 35% to 100% biology base.In one embodiment, formula (Ia), the compound of (Ib) and (Ic)
It is about 50% to 100% biology base.In one embodiment, the compound of formula (Ia), (Ib) and (Ic) be about 75% to
100% biology base.In one embodiment, the compound of formula (Ia), (Ib) and (Ic) is 100% biology base.Formula (Ia),
(Ib) and at least one R, R in each of (Ic)3、R4、R19It is-H to allow to react with isocyanate groups.Compound is put down
Equal OH values can be merely greater than 0 to about 230, preferably about 10 to about 175, and most preferably in the range of about 25 to about 140
It is interior.
In order to prepare the compound of the present invention, by the compound of formula (Ia), (Ib) or (Ic) or their mixture with contain
Isocyanates, diisocyanate, polyisocyanates or their the mixture reaction of isocyanate groups.Containing isocyanate group
The compound of group increases the branched nature of polymer.Term " polyisocyanates " is defined as diisocyanate and higher functional
The isocyanates of change, and the term includes oligomer.Mainly any list with two or more isocyanate groups
Isocyanates or polyisocyanates, or mainly any isocyanide of the polyisocyanates with two or more isocyanate groups
Acid esters precursor is suitable for the present invention.For example, hexamethylene diisocyanate homopolymer is suitable for herein and commercially available.
It should be understood that micro diisocyanate can be retained in the product with multiple isocyanate groups.The example of this respect be containing
The biuret of a small amount of hexamethylene diisocyanate remnants.
Be also suitable as polyisocyanates reactant is the isocyanurate trimer derived from hydrocarbon diisocyanate.It is excellent
Choosing is that DESMODUR N-100 (are based on hexamethylene diisocyanate, derive from Beyer Co., Ltd of Pittsburgh of Pennsylvania
(Bayer Corporation, Pittsburgh, PA)).Other triisocyanates that can be used for the object of the invention are by making three
Mole toluene di-isocyanate(TDI) reaction and obtain those of.The isocyanurate trimer and 3- isocyanides of toluene di-isocyanate(TDI)
Acid group closes methyl -3,4, and the isocyanurate trimer of 4- trimethylcyclohexylisocyanates is can be used for the object of the invention three
The other examples of isocyanates, as methane-three-(phenyl isocyanate).The precursor of polyisocyanates such as diisocyanate
It is also suitable as the base material of polyisocyanates in the present invention.DESMODUR derived from Beyer Co., Ltd of Pittsburgh of Pennsylvania
N-3300, DESMODUR N-3600, DESMODUR Z-4470, DESMODUR H, DESMODUR N3790 and DESMODUR
XP 2410 and double-(4- isocyanatocyclohexyls) methane are also applied in the present invention.
Preferred polyisocyanates reactant is to include the aliphatic series and aromatic polyisocyanate of biuret structure, or comprising different
The dimethyl silicone polymer of cyanate.Such polyisocyanates also includes aliphatic series and aromatic substituent.
What it is particularly preferable as (poly-) isocyanates reactant for all embodiments of the invention is such as conduct
DESMODUR N-100, DESMODUR N-75 and DESMODUR N-3200 are commercially available from Beyer Co., Ltd of Pittsburgh of Pennsylvania
The hexamethylene diisocyanate homopolymer of acquisition；The 3- isocyanos that can be for example obtained as DESMODUR I (Beyer Co., Ltd)
Close methyl -3,4,4- trimethylcyclohexylisocyanates；Double-(the 4- that can be for example obtained as DESMODUR W (Beyer Co., Ltd)
Isocyanatocyclohexyl) methane and formula (IIa), (IIb), (IIc) and (IId) diisocyanate trimer：
Diisocyanate trimer (IIa to IId) can for example as DESMODUR Z4470, DESMODUR IL,
DESMODUR N-3300 and DESMODUR XP2410 are obtained from Beyer Co., Ltd respectively.
In one embodiment, the compound of (a) containing isocyanates and (b) isocyanate-reactive compound react production
Object includes the organic compound that water, formula (IIIa) are further selected from (c)
R5- X (IIIa),
The organic compound of formula (IIIb)
R15-(OCH2CH(OR16)CH2)z-OR17(IIIb),
Or the unreacting isocyanate group of at least one of their mixture second compound reaction, wherein R5Choosing
From-the C for optionally including at least one unsaturated group1To C30The C of linear chain or branched chain alkyl, hydroxy-functional1To C30Straight chain
Or the linear chain or branched chain C of branched hydrocarbyl, hydroxy-functional1To C30Polyethers, the linear chain or branched chain polyester of hydroxy-functional, hydroxyl official
The linear chain or branched chain organosiloxane of energyization, the C of thiol-functional1To C30Linear chain or branched chain alkyl, amine-functionalized C1To C30
Linear chain or branched chain alkyl,
Wherein R7、R8And R9It is each independently-H ,-C1To C6Alkyl or combination thereof；R10For 1 to 20 carbon
Bivalent hydrocarbon radical group；X is isocyanate-reactive functional group such as-OH ,-C (O) OH ,-SH ,-NH (R12)、-O-(CH2CH2O)S
(CH(CH3)CH2O)t- H or-[C (O)]-O- (CH2CH2O)s(CH(CH3)CH2O)t-H；R12For H or unit price C1To C6Alkyl base
Group；R15、R16And R17It is each independently-H；-R18；-C(O)R18；Precondition is at least one R15、R16Or R17For-H；R18
It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain hydrocarbyl group of at least one unsaturated bond；Z be 1 to
15；Y is-Cl；The integer that s is 0 to 50；The integer that t is 0 to 50；S+t is more than 0.As used herein, term " branch " means official
Energy chain can be branched at any point as example quaternary carbon, and may include any number of branched alkyl substituent.
In one embodiment, second compound exist and with the isocyanide of about 0.1 mole of % to about 60 moles of %
Acid esters group reacts.Preferably, the compound concentration of isocyanate-reactive compound (b) is more than second compound (c)
Concentration.
In one embodiment, second compound (c) is water.Water can be used for making unreacted isocyanate group by urea bond
Group's crosslinking.In a further embodiment, second compound (c) has formula (IIIa).The compound of formula (IIIa) can be comprising extremely
The hydrophily water-soluble substance of the hydroxy-end capped polyethers of a few formula (IIIa), wherein isocyanate-reactive group X are-O-
(CH2CH2O)s(CH(CH3)CH2O)t- H or-[C (O)]-O- (CH2CH2O)s(CH(CH3)CH2O)t-H.In this embodiment ,-
(CH2CH2O)-expression ethylene oxide group (EO), and-(CH (CH3)CH2O)-indicate oxypropylene group (PO).These polyethers can wrap
Containing only EO groups, only PO groups or their mixture.These polyethers are alternatively arranged as being expressed as PEG-PPG-PEG (poly- second two
Alcohol-polypropylene glycol-polyethylene glycol) triblock copolymer exist.Preferably, polyethers is the poly- second of commercially available methoxyl group two
Or mixtures thereof alcohol (MPEG),.Also composition commercially available and suitable for the preparation present invention is containing equal weight
Ethylene oxide group and oxypropylene group (Union Carbide Corporation's (Union Carbide Corp.) 50-HB series UCON fluids and
Lubricant) and average molecular weight be greater than about 1000 butoxy polyoxyalkylene.The hydroxyl terminated polyether of formula (IIIa) is averaged
Molecular weight is preferably equal to or greater than about 200, and most preferably between 350 and 2000.
In another embodiment, second compound (c) is the organic compound of formula (IIIa), and wherein isocyanates reacts
Property group X be-OH ,-C (O) OH ,-SH ,-NH (R12)；And R5Selected from-the C for optionally including at least one unsaturated group1
To C30The C of linear chain or branched chain alkyl, hydroxy-functional1To C30The linear chain or branched chain C of linear chain or branched chain alkyl, hydroxy-functional1
To C30Polyethers, the linear chain or branched chain polyester of hydroxy-functional, hydroxy-functional or the organic silica of amine-functionalized linear chain or branched chain
The C of alkane, thiol-functional1To C30Linear chain or branched chain alkyl, amine-functionalized C1To C30Linear chain or branched chain alkyl.
In the case where isocyanate-reactive group X is-OH, the example of formula (IIIa) includes but not limited to that hydrocarbon alcohol is all
Such as propyl alcohol, butanol or fatty alcohol (R including stearyl alcohol5To include-the C of at least one unsaturated group1To C30Straight chain or branch
Chain alkylene)；Hydrocarbon based diol or polyalcohol such as ethylene glycol, propylene glycol, butanediol or hexylene glycol (R5For the C of hydroxy-functional1Extremely
C30Linear chain or branched chain alkyl)；Alkylene glycol ether such as triethylene glycol, tetraethylene glycol, poly(ethylene glycol) (PEG), poly- (the third two
Alcohol) (PPG), poly- (tetrahydrofuran) or the mixture with PEG, PPG or THF unit glycol ethers (R5For hydroxy-functional
Linear chain or branched chain C1To C30Polyethers)；Polyester polyol (R5For the linear chain or branched chain polyester of hydroxy-functional)；Silicone prepolymer is more
First alcohol (R5For the linear chain or branched chain organosiloxane of hydroxy-functional)；N, N- dimethylaminoethanol (R5For amine-functionalized C1
To C30Linear chain or branched chain alkyl)；Choline chloride or betaine HCl (R5For Y-(R7)(R8)(R9)N+R10-)；Diacetylmonoxime (R5For
(R7)(R8) C=N-).Polyether polyol may include only EO groups, only PO groups, only THF groups or their mixture.These
Polyethers is alternatively arranged as block copolymer presence, is such as indicated by PEG-PPG-PEG (polyethylene glycol propylene glycol-polyethylene glycol)
Block copolymer.Preferably, the average molecular weight of polyetherdiol is equal to or greater than about 200, and most preferably 350 with
Between 2000.
In the case where isocyanate-reactive group X is-C (O) OH, the example of formula (IIIa) includes but not limited to fat
Sour such as octanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, palm
Oleic acid, linoleic acid, arachidonic acid, oleic acid or erucic acid (R5Optionally to include the-C of at least one unsaturated group1To C30
Linear chain or branched chain alkyl)；Hydroxyl-containing acid such as Hydroxyoctanoic acid, hydroxydecanoic acid, hydroxylauric acid, hydroxymyristic acid, hydroxyl palm
The sub- oil of acid, hydroxy stearic acid, hydroxyarachidic acid, hydroxyl behenic acid, hydroxyl tetracosane acid, hydroxyl palmitoleic acid, hydroxyl
Acid, hydroxyeicosatetraenoic acid, hydroxy oleate or hydroxyl erucic acid (R5For the C of hydroxy-functional1To C30Linear chain or branched chain alkyl)；
And mercaptoalkanoic acid such as mercaptopropionic acid (R5For the C of thiol-functional1To C30Linear chain or branched chain alkyl).
In the case where isocyanate-reactive group X is-SH, the specific example of formula (IIIa) includes but not limited to alkyl
Mercaptan such as lauryl mercaptan or lauryl mercaptan (R5Optionally to include the-C of at least one unsaturated group1To C30Directly
Chain or branched hydrocarbyl).It is-NH (R in isocyanate-reactive group X12) in the case of, the specific example of formula (IIIa) include but
It is not limited to alkylamine such as diisopropylamine, propylamine, hexylamine or lauryl amine (R5For optionally comprising at least one unsaturated group
- C1To C30Linear chain or branched chain alkyl)；Alkanolamine such as ethanol amine or Propanolamine (R5For the C of hydroxy-functional1To C30Directly
Chain or branched hydrocarbyl)；Silicone prepolymer polyamine (R5For amine-functionalized linear chain or branched chain organosiloxane)；Alkyl diamines (R5For
Amine-functionalized C1 to C30 linear chain or branched chains alkyl)；And amidoalkanesulfonic acid such as 2-aminoethanesulfonic acid (R5For HO-S (O)2R10-)。
In a further embodiment, second compound (c) has formula (IIIb).These compounds are commonly known as poly- sweet
Oil.These polyglycereol may be present, wherein R15、R16And R17It is each independently-H；-R18；-C(O)R18；Precondition is at least
One R15、R16Or R17For-H, and wherein R18It independently is with 5 to 29 carbon and optionally includes that at least one is unsaturated
The linear chain or branched chain hydrocarbyl group of key.Specific example include but not limited to triglycerin monostearate, triglycerin distearate,
Six glyceryl monostearates, six glycerol distearates, ten glycerine lists (caprylate/decylate), ten glycerine, the two (caprylate/last of the ten Heavenly stems
Acid esters), ten glycerine, polyglycereol -3 and C18 diglycerides.
In one embodiment, the compound of (a) containing isocyanates and (b) isocyanate-reactive compound react production
Object includes further to be reacted not with multiple second compounds (c) of the compound comprising formula (IIIa) or (IIIb) and both water
Isocyanate reaction group.
The compound of the present invention can be prepared with a step.Include formula (Ia), (Ib) or (Ic) more than one of the present invention
The compound of kind organic compound and/or one or more second compounds (c) can also a step preparation.Preferably, such as
More than one organic compound and/or one or more second compound (c) of the fruit using formula (Ia), (Ib) or (Ic), then may be used
Synthesis is completed in order.When using the compound of the formula (Ia), (Ib) or (Ic) with high OH numbers, or works as and use more officials
When energy compound (c), sequence addition is particularly useful.These steps include make (a) be selected from isocyanates, diisocyanate,
The compound of at least one of polyisocyanates or their mixture containing isocyanate groups, and (b) be selected from formula (Ia),
(Ib) or at least one of (Ic) or their mixture isocyanate-reactive compound react, wherein each R is independent
Ground is-H；-R1；
-C(O)R1；-(CH2CH2O)n(CH(CH3)CH2O)mR2；Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；Each
N is independently 0 to 20；Each m is independently 0 to 20；M+n is more than 0；Each R1It independently is with 5 to 29 carbon and optional
Ground includes the linear chain or branched chain hydrocarbyl group of at least one unsaturated bond；Each R2It independently is-H or there are 6 to 30 carbon simultaneously
Optionally include the linear chain or branched chain hydrocarbyl group of at least one unsaturated bond, precondition is when compound is formula (Ia), then
R or R2At least one of be-H；Each R3It independently is-H；-R1；-C(O)R1；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；
Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；Each R4It independently is-H, there are 6 to 30 carbon and optionally include extremely
The linear chain or branched chain hydrocarbyl group or combination thereof of few 1 unsaturated bond；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-
(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；Each n ' is independently 0 to 20；Each m ' is independently 0 to 20；M '+n ' is big
In 0；Precondition is then at least one R when compound is formula (Ib)2、R3Or R4For-H；And each R19For-H ,-C (O)
R1Or-CH2C[CH2OR]3, precondition is then at least one R when compound is formula (Ic)19Or R is-H.When using second
When compound (c), the molar concentration of at least one compound selected from formula (Ia), (Ib) or (Ic) makes unreacted isocyanide
There are still to be reacted with one or more second compounds (c) for acid esters group.
Make at least one isocyanates, diisocyanate, polyisocyanates or their mixture, and is selected from isocyanide
Compound of at least one of acid esters, diisocyanate, polyisocyanates or their mixture containing isocyanate groups,
(b) it is anti-that formula (Ia), (Ib) or at least one of (Ic) or their mixture isocyanate-reactive compound are selected from
It answers.The reaction usually by by isocyanates, diisocyanate or polyisocyanates and selected from formula (Ia), (Ib) or (Ic),
Or at least one of their mixture compound, and optionally second compound (c) is packed into reaction vessel to carry out.Reagent
The sequence of addition is not crucial, but if using water, water should in isocyanates and selected from formula (Ia), (Ib) or (Ic) or
It is added after the reaction of at least one of their mixture compound.
The specific weight for the reactant being packed into is adjusted based on their equivalent and the displacement volume of reaction vessel
It saves into and the compound selected from formula (Ia), (Ib) or (Ic) will be consumed in the first step.Usually using without isocyanide
The suitable dry organic solvent of acid esters group reactive group is as solvent.Ketone is preferred solvent, and for convenience
And availability, methyl iso-butyl ketone (MIBK) (MIBK) is particularly preferred.Stirring is packed into object, and temperature is adjusted to about 40 DEG C to 70
℃.In general, then the amount of about 0.01 to about 1.0 weight % adds urge in organic solvent usually in terms of the dry weight based on composition
Agent such as iron chloride (III), and temperature is increased to about 80 DEG C to 100 DEG C.Co-catalyst, such as sodium carbonate also can be used.
If being added to water, initial reaction is carried out so that the isocyanate groups less than 100% react.Keep several hours it
In second step afterwards, other solvent, water and optional second compound (c) are added, and allow mixture stoichiometric number small
When or until all isocyanates have reacted.
In another embodiment, the present invention is the composition for assigning base material water-resistance and optional soil release performance, should
Composition includes the aqueous solution or dispersion of at least one compound prepared by following steps：Make (a) be selected from isocyanates,
Compound of at least one of diisocyanate, polyisocyanates or their mixture containing isocyanate groups, and (b)
At least one isocyanate-reactive compound reaction selected from formula (Ia), (Ib) or (Ic).The composition includes the present invention's
At least one compound and solvent or water, and choose any one kind of them or a variety of surfactants.Prepare the present invention aqueous solution or
During dispersion, if it is desired, other water can be added to carbamate compounds together with surfactant, and
And stirring is until being thoroughly mixed.After homogenizing or ultrasound treatment step, organic solvent can be removed by vacuum distillation, and remaining
The compound of the present invention aqueous solution or dispersion can use as it is, or be further processed.
Other than compound as of the invention described herein, these compositions also may include by commercially available mountain
The compound that pears sugar alcohol, polysorbate, alkyl citrate or pentaerythrite provide.These compounds may be present as from complete
The complete unsubstituted various substituted organic compounds to the formula that is completely replaced (Ia), (Ib) or (Ic) and various substitutions therebetween
Base, and optionally, there are 5 to 29 carbon and include the mixture of the linear chain or branched chain hydrocarbyl group of at least one unsaturated bond.
It will be apparent to those skilled in the art that also can be used to a variety of of any or all of above process
Variation, will obtain the Optimization of reaction condition of highest yield, productivity or product quality.
In another embodiment, the present invention is the method for the treatment of of fibrous substrates, and this method includes being applied to the surface of base material
Add the compound prepared by following steps：So that (a) is selected from isocyanates, diisocyanate, polyisocyanates or theirs is mixed
The compound of at least one of object containing isocyanate groups is closed, and (b) is selected from formula (Ia), (Ib) or (Ic) or theirs is mixed
The isocyanate-reactive compound reaction of at least one of object is closed, wherein each R independently is-H；-R1；-C(O)R1；-
(CH2CH2O)n(CH(CH3)CH2O)mR2；Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；Each n is independently 0 to 20；Often
A m is independently 0 to 20；M+n is more than 0；Each R1It independently is with 5 to 29 carbon and optionally includes at least one insatiable hunger
With the linear chain or branched chain hydrocarbyl group of key；Each R2It independently is-H or with 6 to 30 carbon and optionally comprising at least one
The linear chain or branched chain hydrocarbyl group of unsaturated bond；Precondition is the then R or R when compound has formula (Ia)2In at least one
A is-H；Each R3It independently is-H；-R1；-C(O)R1；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’
(CH(CH3)CH2O)m’C(O)R1；Each R4It independently is-H, there are 6 to 30 carbon and optionally includes at least one unsaturated bond
Linear chain or branched chain hydrocarbyl group or combination thereof；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’(CH
(CH3)CH2O)m’C(O)R1；Each n ' is independently 0 to 20；Each m ' is independently 0 to 20；M '+n ' is more than 0；Precondition
It is then at least one R when compound is formula (Ib)2、R3Or R4For-H；And each R19For-H ,-C (O) R1Or-CH2C
[CH2OR]3, precondition is then at least one R when compound is formula (Ic)19Or R is-H, the compound connects to it
Tactile base material provides water-resistance and optional soil release performance.
By any suitable method, compound or composition present invention as described above is made to be contacted with base material.It is such
Method includes but not limited to be applied by mode as described below：Exhaustion, foam, elastic bite, bite, pad, wet roll, rolling
Forging, hank knotting, capstan winch, liquid injection, overflow, roller, brush, roller, spraying, dipping, submergence etc..Can also by using cylinder contaminate method,
Continuous dyeing method or spinning line application contact the composition.
The compound of the present invention or composition itself are applied to base material, or by its textile fabric finishing agent optional with other
Or the combination of surface conditioning agent is applied to base material.Such optional annexing ingredient includes the processing for obtaining additional surface effect
Agent or finishing agent, or the additive that is usually used together with such inorganic agent or finishing agent.Such annexing ingredient includes providing table
The compound or composition of face effect, the surface effect such as easy-care properties, easily scald property, shrink control, it is wrinkle-free, it is durable pressure press,
Moisture control, flexibility, intensity, skid resistance, static electricity resistance, anti-snag wound property, anti pilling property, soil release performance, anti-tartar, detergency,
Water-resistance, smell control, microbial resistance, sun protection, cleanablity and similar effect.It can be in the combination for applying the present invention
Before, after or at the same time, one or more such inorganic agents or finishing agent are applied on base material for object.For example, for fiber base
For material, when handling synthetic textiles or cotton fabric, it may be desired using wetting agent, it is bright to be such as available from Delaware State prestige
E.I.Du Pont De Nemours and Co. of city (E.I.du Pont de Nemours and Company, Wilmington, DE)
ALKANOL 6112.When handling cotton fabric or cotton mixed fabric, crease-resistant resin can be used, be such as available from the South Carolina and cut
The PERMAFRESH EFC of Si Teounuofa companies (Omnova Solutions, Chester, SC).
Usual other additives being used together with such inorganic agent or finishing agent, such as surface-active can be also optionally present
Agent, pH adjusting agent, crosslinking agent, wetting agent, wax extender and other additives well known by persons skilled in the art.Suitably
Surfactant includes anion surfactant, cationic surfactant, nonionic surfactant, N- oxides and two
Property surfactant.The example of such additives includes processing aid, foaming agent, lubricant, anti-fouling agent etc..Composition is manufacturing
Apply at factory, retail point, or installing and using preceding application, or applies at consumer place.
Optionally, addition blocked isocyanate and composition of the invention to further increase durability (that is, as being blended
Composition).Example for the suitable blocked isocyanate in the present invention is to be available from Utah State salt lake city Huntsman Corporation
The PHOBOL XAN of (Huntsman Corp, Salt Lake City, UT).Other commercially available blocked isocyanates
It is applicable in this article.The required property that blocked isocyanate is added depends on the specific application of copolymer.For most of current pre-
For the application thought, do not need its exist can be obtained between chain satisfactorily crosslinking or and base material combination.When as altogether
When mixed isocyanates adds, the amount of addition is up to about 20 weight %.
Optimization process for giving base material depends on (1) the compound of the present invention or the characteristic of composition, (2) base material
Surface characteristic, (3) are applied to the compound of the present invention on surface or the amount of composition, and (4) are by the compound of the present invention or combination
Object is applied to method and many other factors on surface.Some compound or compositions of the present invention are in many different bases
It plays a role well on material and water resistant.Usually by spraying, impregnate, pad or other well-known process, will be by the present invention's
Dispersion prepared by compound is applied on fiber base material.After for example by compression roller by excessive liquid removal, it will locate
The fiber base material of reason is dried, then by being heated to for example, about 100 DEG C to about 190 DEG C at least 30 seconds, normally about 60 seconds to about 240
Second cures.The durability of such solidification enhancing grease resistance, water-resistance and anti-tartar and the resistance.Although these cure
Condition is typical, but some business equipment can be operated because its specific design feature is different except these ranges.
In another embodiment, the present invention is with the compound or composition as described above being applied on its surface
Fiber base material.The invention also includes the base materials handled with compound or composition present invention as described above.Suitable base
Material includes fiber base material.Fiber base material include fiber, yarn, fabric, fabric blends, textile fabric, non-woven material, paper,
Leather and carpet.These can be prepared by naturally occurring or synthetic fiber, and the fiber includes cotton, cellulose, wool, silk, artificial silk, Buddhist nun
Dragon, aromatic polyamides, cellulose acetate, acrylic fiber, jute, sisal hemp, sea grass, coir fibre, polyamide, polyester, polyene
Hydrocarbon, polyacrylonitrile, polypropylene, Nomex or their blend.So-called " fabric blends " mean by two or more
Fabric made of the fiber of type.These usual blends are the groups of at least one natural fiber and at least one synthetic fibers
It closes, but may also comprise the blend of two or more natural fibers or the blend of two or more synthetic fibers.It is non-
Woven substrates include such as spunlaced nonwoven object, are such as available from E.I.Du Pont De Nemours and Co. of Delaware State Wilmington city
SONTARA and spunbond-melt blown-spunbond non-woven fabric.The base material of the processing of the present invention has excellent water-resistance and appoints
Select soil release performance characteristic.
The compound of the present invention, composition, method and base material can be used for the base material of processing provide excellent water-resistance with
And optional soil release performance.Surface characteristic is obtained using nonfluorinated silylorganocarbamate as described above.It has been found that using nonfluorinated
Silylorganocarbamate provides more excellent water-resistance and durable water-resistance compared with traditional nonfluorinated water repellent agent, and can be with
Commercially available fluorination water repellent agent is compared.The base material of the processing of the present invention can be used in a variety of applications and product, such as clothes,
Protective garment, carpet, furniture upholstery, furnishings and other purposes.It is clear that above-mentioned excellent surface characteristic helps to maintain surface
It is clean, therefore allow more muchly to use.
Test method and material
Unless otherwise specified, all solvents and reagent are purchased from St. Louis Sigma-Aldrich public affairs
It takes charge of (Sigma-Aldrich, St.Louis, MO), and is directly used by the original sample of supply.1000 quilt of MPEG 750 and MPEG
It is respectively defined as poly(ethylene glycol) methyl ether 750 and poly(ethylene glycol) methyl ether 1000, and can be from St. Louis
Sigma-Aldrich is commercially available.TMN-10 can be from St. Louis Sigma-Aldrich
Company is commercially available.
D-sorbite tristearate and sorbitan monostearate can from Britain east Yorkshire standing grain major company (Croda,
East Yorkshire, England) or the nutrition of Copenhagen, Denmark Du Pont and health company (DuPont Nutrition＆
Health, Copenhagen, Denmark) it is commercially available.Low OH D-sorbites tristearate (OH values ＜ 65), two seasons penta 4
Alcohol ester, sorbitol ester-lauric acid, D-sorbite tribehenin essence 40, D-sorbite tribehenin essence 50, D-sorbite tribehenin essence
88 and glycerol distearate derive from the nutrition of Copenhagen, Denmark Du Pont and healthy company.
DESMODUR N-100、DESMODUR H、DESMODUR I、DESMODUR N3300、DESMODUR N3790BA、
DESMODUR Z4470 and DESMODUR XP2410 derive from Beyer Co., Ltd of Pittsburgh of Pennsylvania.
JEFFAMINE M-1000, JEFFAMINE M-2070 and PHOBOL XAN are stepped derived from Utah State salt lake city Hensel
Company.
PRIPOL 2033 (amorphous dimer diols), PRIAMINE 1075 (dimer diamine), PRIPLAST 3293
(semicrystalline polyester polyalcohol), D-sorbite trioleate, polyoxyethylene sorbitol tristearate, polyoxyethylene sorbitol
Alcohol trioleate, tetraethoxy sorbitan monostearate, polyoxyethylene sorbitol monostearate and polyoxyethylene
(4) sorbitan monostearate derives from Britain east Yorkshire standing grain major company.
Three (2- octadecyls) citrates can from Ohio Wyclif Lubrizol Corp. (Lubrizol,
Wickliffe, Ohio) it is commercially available.
SILMER OH Di-10 (the Bifunctionalized hydroxy-end capped silicone prepolymer of small straight chain) and SILMER NH Di-8
(linear chain silicones with reactive amine end group) are available from Toronto Siltech company (Siltech
Corporation, Toronto, Canada).
PLURONIC L35 can be from Ludwigshafen, Germany BASF AG (BASF, Ludwigshafen, Germany) quotient
Purchase obtains.ARMEEN DM-18D derive from New Jersey Bridgwater Akzo Nobel N.V. (Akzo-Nobel,
Bridgewater, NJ).
Triglycerin monostearate and six glycerol distearates derive from New Jersey Allendale Long Sha companies (Lonza,
Allendale, NJ).
Ten glycerine lists (caprylate/decylate) derive from Illinois Northey Field Si Taipan companies (Stepan,
Northfield, Illinois).
Polyglycereol -3 derive from Texas Houston Su Wei chemical companies (Solvay Chemicals, Houston,
TX)。
In the example of this paper, following test method and material are used.
Test method 1- water-resistance
(Global Specifications and Quality are tested according to the whole world Teflon specification and quality control
Control Tests) Du Pont's technology experiment room method for summarizing in packet, measure the water-resistance of handled base material.The survey
Examination measures resistance of the base material for liquid, aqueous wetability of processing.The water-alcohol mixture drop of different surfaces tension is placed in and is knitted
On object, and vision determines the degree of moistened surface.The test provides resistance to water spotting rough index.Water-resistance grade is got over
Height, the resistance that final base material pollutes water-based material are better.The composition of standard test liquid is shown in the following table 1.For being more than
The test liquid of critical value is determined by subtracting half from the number in table 1 with 0.5 incremental grade.
1. standard test liquid of table
Test method 2- spray tests
The dynamic water-resistance of the base material of processing is measured according to American Association of Textile Chemists and Colorists (AATCC) TM-22.Ginseng
The standard for examining announcement carries out visual score using the grade 100 of the no water penetration of instruction or surface adhesion to sample.Grade 90
Indicate slight random adherency or the wetting without infiltration；Lower value instruction gradually increased wetting and infiltration.Test method 2,
I.e. dynamic water-resistance is tested, and is the harshness of water-resistance and true test.
Test method 3- soil release performance
The measurements determination fabric removes the ability of oil stain during home washings.
The textile fabric of processing is placed on flat surfaces.Using dropper, by 5 drop MAZOLA corn oils or mineral oil
(0.2mL) is placed on fabric to form 1 oil dripping.Weight (5Ib, 2.27kg) is placed in oil droplet with a glassine paper of separation oil droplet
Top on.Weight is left in place 60 seconds.After 60 seconds, weight and glassine paper are removed.Then joined by 1993 standards of AATCC
Detergent WOB12 or detergent granules (100g) are examined, are up to the washing of textile fabric sample 12 minutes using autowash.So
Textile fabric drying is up to 45-50 minutes afterwards.Then be directed to residual stains by textile fabric be evaluated as 1 to 5,1 have it is remaining most
Big residual stains, and 5 be no visible residual stains.
Test method 4- fabric treatings
The fabric handled in this study is the tin Lay Asia-Pacific Lars spinning for being available from 29732 Rock Hill of the South Carolina
Fabric test Solution company (SDL Atlas Textile Testing Solutions, Rock Hill, South
Carolina 100 weight % khaki cotton twills) and be available from L.Michael OY companies of Finland (L.Michael OY,
Finland) 100% weight % red polyester textiles.Using conventional pad bath (dipping) method, with various emulsion polymers
Aqueous dispersion handles fabric.The masterbatched dispersion that obtained polymer emulsion is diluted with deionized water, to realize described
Pad bath with the final lotions of 60g/L or 100g/L in bath.
The example of the compound of the present invention and composition is organised by various isocyanates and formula (Ia), (Ib), (Ic)
It closes object or is prepared by their mixture.The present invention is not limited by the following sample.
The preparation of three (octadecyl) citrates
In 4 neck round-bottom flasks for being equipped with overhead type stirrer, thermocouple, dean-stark/ condensers, addition is stearic
Alcohol (100.0g), citric acid (20g), toluene (150g) and sulfuric acid (2g).Solution flows back 8 hours in order to removing during esterification
The water of generation.After 8 hours, crude citrate is precipitated, filtered and recrystallized at 0 DEG C using ethyl alcohol.
Example 1
In 4 neck round-bottom flasks for being equipped with overhead type stirrer, thermocouple, dean-stark/ condensers, sorb is added
Sugar alcohol tristearate (116.0g, hydroxyl value=77.2mgKOH/g) and 4-methyl-2 pentanone (MIBK, 150g).Solution is set to return
1 hour is flowed to remove any residual moisture.After the hour, solution is cooled to 50 DEG C, addition DESMODUR N-100
(30g) then adds catalyst, and solution is heated to 80 DEG C and is surpassed after an hour.
Example 2
Prepare the aqueous dispersion of the compound as described in example 1.By water (300g), ARMEEN DM-18D (5.6g),
TERGITOL TMN-10 (2.8g) and acetic acid (3.4g) are added in beaker and stir to form surfactant solution.It will
Solution is heated to 60 DEG C.The D-sorbite such as prepared in example 1 carbamate/MIBK solution is cooled to 60 DEG C and is delayed
Slow addition surfactant solution is to generate creamy emulsion.Mixture is homogenized at 6000psi, and gained lotion is being subtracted
Distillation is to remove solvent under small pressure, to generate nonflammable urethane dispersion with 25% solid.By the amino
Formic acid ester dispersion is applied to textile fabric and is tested according to above-mentioned test method.
Example 3 to 23
Example 3 to 23 illustrates to use isocyanates as described in example 1 (compound) and example 2 (dispersion)
One or more different compound such as D-sorbite tristearate, the D-sorbites of (DESMODUR N100) and formula (Ia)
The various compounds of the present invention prepared by trioleate, sorbitan monostearate and their mixture.When using not
Only when a kind of sorbitol ester reagent, the second D-sorbite reagent is added, and reaction mixture is heated additionally at 80 DEG C
Four hours.Example 3 to 23 is applied to textile fabric with 60g/L as dispersion, and is tested according to above-mentioned test method.
Comparative examples A
Comparative examples A indicates the moisture content that the compound using formula (Ia) is prepared in the case of no isocyanate compound
Granular media.Water (166.0g), ARMEEN DM-18D (2.29g), TERGITOL TMN-10 (1.6g) and acetic acid (1.4g) are added
To in beaker and stir to form surfactant solution.Solution is heated to 60 DEG C.By D-sorbite tristearate
(60.52g, hydroxyl value=69.5mgKOH/g) is heated to 80 DEG C, and is slowly added surfactant solution to generate emulsus breast
Liquid.Mixture is homogenized at 6000psi, and gained lotion is distilled under reduced pressure to remove solvent, thus with
25% solid generates nonflammable dispersion.The dispersion is applied to textile fabric and is surveyed according to above-mentioned test method
Examination.
The composition of 2. example 2 to 23 of table
The performance data of table 3. example 2 to 23 and Comparative examples A
Example 24 to 31
Example 24 to 31 follows the process of example 1 (compound) and example 2 (dispersion), using each as described in table 4
A kind of to two kinds different compounds of kind isocyanates and formula (Ia).When using the compound of more than one formula (Ia), addition
Second compound, and reaction mixture is heated additional four hours at 80 DEG C.By example 24 to 31 as dispersion with
60g/L is applied to textile fabric, and is tested according to above-mentioned test method.
The composition of 4. example 24 to 31 of table
The performance data of 5. example 24 to 31 of table
Example 32 to 36
Example 32 to 36 follows the process of example 1 (compound) and example 2 (dispersion), using as described in table 6
DESMODUR N-100 isocyanates, a kind of to two kinds different compounds of formula (Ia) and acid monomers.Example 36 further includes hard
Lipidol monomer.After the precursor compound and isocyanates of formula (Ia) have reacted 1 hour, by acid monomers, stearyl alcohol and formula
(Ia) any other compound is added in reaction, and reaction mixture is heated additional four hours at 80 DEG C.It will
Example 32 to 36 is applied to textile fabric as dispersion with 60g/L, and is tested according to above-mentioned test method.
The composition of 6. example 32 to 36 of table
The performance data of 7. example 32 to 36 of table
Example 37 to 54
Example 37 to 54 follows the process of example 1 (compound) and example 2 (dispersion), using different as described in table 8
Cyanate, a kind of to two kinds different compounds of formula (Ia) and MPEG 750.In the precursor compound and isocyanic acid of formula (Ia)
After ester has reacted 1 hour, any other compound of MPEG 750 and formula (Ia) is added in reaction, and will reaction
Mixture heats additional four hours at 80 DEG C.Example 37 to 54 is applied to textile fabric, and root as dispersion with 60g/L
It is tested according to above-mentioned test method.
The composition of 8. example 37 to 54 of table
The performance data of 9. example 37 to 54 of table
Example 55 to 62
Example 55 to 62 follows the process of example 1 (compound) and example 2 (dispersion), using as described in table 10
DESMODUR N-100 isocyanates, D-sorbite tristearate, ethylene glycol or alkoxylated monomers, and up to one kind
Other reagent.After the precursor compound and isocyanates of formula (Ia) have reacted 1 hour, by ethylene glycol or alkoxylate list
Body and other reagent are added in reaction, and reaction mixture is heated additional four hours at 80 DEG C.By example 55 to
62 are used as dispersion to be applied to textile fabric with 60g/L, and are tested according to above-mentioned test method.
The composition of 10. example 55 to 62 of table
The performance data of 11. example 55 to 62 of table
Embodiment 63 and 64
Example 63 and 64 follows the process of example 1 (compound) and example 2 (dispersion), using as set forth in table 12
DESMODUR N-100 isocyanates, alkoxylated sorbitol ester, and up to a kind of other reagent.In formula (Ia)
After precursor compound and isocyanates have reacted 1 hour, other reagent is added in reaction, and by reaction mixture
It is heated at 80 DEG C additional four hours.Example 63 and 64 is applied to textile fabric as dispersion with 60g/L, and according to above-mentioned
Test method is tested.
Example 65
Example 65 using as set forth in table 12 DESMODUR N-100 isocyanates, alkoxylated sorbitol ester and
MPEG 750.Tetraethoxy sorbitan monostearate (0.8g) and 8.5g 4-methyl-2 pentanones (MIBK) are packed into and placed
On hot plate/blender and it is equipped in nitrogen pipe and the 40mL scintillation vials of stirring rod.Solution is stirred under a nitrogen and is added
Heat continues 10 minutes to 55 DEG C.It adds Desmodur N-100 (1.7g) and reaction temperature is increased to 80 DEG C.Add 0.5 weight
It measures % iron chloride (III) solution (in MIBK) and reaction temperature is increased to 95 DEG C.After six hours, MPEG is added
750(4.5g).Reaction temperature is reduced to 80 DEG C and is stirred overnight.Gained mixture is standardized as 25% solid, with 60g/L
It is applied to textile fabric and is tested according to above-mentioned test method
Example 66 to 69
Example 66 to 69 follows the process of example 65, using as set forth in table 12 DESMODUR N-100 isocyanates,
Alkoxylated sorbitol ester, and up to a kind of other reagent.Formula (Ia) precursor compound and isocyanates
After reaction 6 hours, other reagent is added in reaction, and reaction mixture is heated overnight at 80 DEG C.It will be real
Example 66 to 69 is applied to textile fabric as dispersion with 60g/L, and is tested according to above-mentioned test method.
The composition of 12. example 63 to 69 of table
The performance data of 13. example 63 to 69 of table
Example 70 to 94
Example 70 to 94 follows the process of example 1 (compound) and example 2 (dispersion), different using as set forth in table 14
Cyanate, the compound of formula (Ia), at least one alcohol reagent, and up to a kind of other reagent.In the initial of formula (Ia)
After compound and isocyanates have reacted 1 hour, alcohol reagent and other reagent are added in reaction, and reaction is mixed
Object is closed to heat at 80 DEG C additional four hours.In example 88 to 91, before reactions by sodium carbonate (0.5% total reagent weight)
It is mixed with D-sorbite tristearate.Example 70 to 94 is applied to textile fabric as dispersion with 60g/L, and according to upper
Test method is stated to be tested.
Example 95
Example 95 follows the process of example 65, uses DESMODUR N-100 isocyanates, sorb as set forth in table 14
Sugar alcohol tristearate and PRIPOL 2033.It, will after the precursor compound and isocyanates of formula (Ia) have reacted 6 hours
PRIPOL 2033 is added in reaction, and reaction mixture is heated overnight at 80 DEG C.By example 93 as dispersion with
60g/L is applied to textile fabric, and is tested according to above-mentioned test method.
The composition of 14. example 70 to 95 of table
The performance data of 15. example 70 to 95 of table
Example 96 to 102 and 108 to 110
Example 96 to 102 and 108 to 110 follow example 1 (compound) and example 2 (dispersion) process, use such as table
One or more compounds of DESMODUR N-100 isocyanates, formula (Ia) or formula (Ib) described in 16, and at least one
The other reagent of kind.After the precursor compound and isocyanates of formula (Ia) and (Ib) have reacted 1 hour, by other reagent
It is added in reaction, and reaction mixture is heated additional four hours at 80 DEG C.Example 96 to 102 and 108 to 110 conducts
Dispersion is applied to textile fabric with 60g/L, and is tested according to above-mentioned test method.
Example 103 to 107
Example 103 to 107 follows the process of example 65, uses the DESMODUR N-100 isocyanic acids as described in table 16
Ester, one or more compounds of formula (Ia) or formula (Ib) and at least one other reagent.Formula (Ia) and (Ib) just
After beginning compound and isocyanates have reacted 6 hours, other reagent is added in reaction, and reaction mixture is existed
It is heated overnight at 80 DEG C.In instance 105, before isocyanates addition that sodium carbonate (0.07g) and D-sorbite three is stearic
Acid esters and the mixing of D-sorbite citrate.Example 103 to 104 and 106 to 107 applies (example as dispersion with 60g/L
105 are applied with 100g/L) textile fabric is arrived, and tested according to above-mentioned test method.
The composition of 16. example 96 to 110 of table
The performance data of 17. example 96 to 110 of table
Example 111 to 114
Example 111 to 114 follows the process of example 1 (compound) and example 2 (dispersion), using as described in table 18
DESMODUR N-100 isocyanates, one or more compounds of formula (Ia) and at least one other reagent.In formula
(Ia) after precursor compound and isocyanates has reacted 1 hour, other reagent is added in reaction, and will reaction
Mixture heats additional four hours at 80 DEG C.Example 111 to 114 is applied to textile fabric as dispersion with 60g/L, and
It is tested according to above-mentioned test method.
Example 115 to 117
Example 115 to 117 follows the process of example 65, uses the DESMODUR N-100 isocyanic acids as described in table 18
Ester, one or more compounds of formula (Ia) and at least one other reagent.In the precursor compound and isocyanide of formula (Ia)
After acid esters has reacted 6 hours, other reagent is added in reaction, and reaction mixture is heated at 80 DEG C
Night.Example 115 to 117 is applied to textile fabric with 60g/L as dispersion, and is tested according to above-mentioned test method.
The composition of 18. example 111 to 117 of table
The performance data of 19. example 111 to 117 of table
Example 118
Example 118 follows the process of example 1 (compound) and example 2 (dispersion), makes DESMODUR N- according to table 20
100 isocyanates are reacted with D-sorbite tristearate, and mix sodium carbonate during the reaction as co-catalyst
(0.375g).Example 118 is applied to textile fabric with 60g/L as dispersion, and is tested according to above-mentioned test method.
Embodiment 119 and 120
Example 119 and 120 follows the process of example 65, uses the DESMODUR N-100 isocyanic acids as described in table 20
Ester, D-sorbite tristearate and lauric acid.After the precursor compound and isocyanates of formula (Ia) have reacted 6 hours,
Lauric acid is added in reaction, and reaction mixture is heated overnight at 80 DEG C.By example 119 and 120 as dispersion
Body is applied to textile fabric with 100g/L, and is tested according to above-mentioned test method.
The composition of 20. example 118 to 120 of table
The performance data of 21. example 118 to 120 of table
Example 121 to 124
Example 121 to 124 follows the process of example 65, uses the DESMODUR N-100 isocyanic acids as described in table 22
Ester, D-sorbite tristearate and other reagent.It has been reacted 6 hours in D-sorbite tristearate and isocyanates
Later, other reagent is added in reaction, and reaction mixture is heated overnight at 80 DEG C.By example 121 to 124
Textile fabric is applied to 60g/L as dispersion, and is tested according to above-mentioned test method.
The composition of 22. example 121 to 124 of table
The performance data of 23. example 122 to 125 of table
Example 125 to 131
Example 125 to 131 follows the process of example 65, uses DESMODUR N-100 isocyanic acids as set forth in table 24
Ester, D-sorbite tristearate and other reagent.It has been reacted 6 hours in D-sorbite tristearate and isocyanates
Later, other reagent is added in reaction, and reaction mixture is heated overnight at 80 DEG C.For example 130 to
132, sodium carbonate (0.075g) is included in isocyanates and D-sorbite tristearate reaction process.By example
125 to 131 are used as dispersion to be applied to textile fabric with 60g/L (example 125 to 128) or 100g/L (example 129 to 131), and
And it is tested according to above-mentioned test method.
Example 132
Example 132 follows the process of example 1 (compound) and example 2 (dispersion), using as set forth in table 24
DESMODUR N-3300 isocyanates, two kinds of compounds of formula (Ia) and C18 diglycerides.In the initial chemical combination of formula (Ia)
After object and isocyanates have reacted 1 hour, C18 diglycerides and sorbitan monostearate are added in reaction, and
And reaction mixture is heated additional four hours at 80 DEG C.Example 132 is applied to textile fabric as dispersion with 60g/L,
And it is tested according to above-mentioned test method.
The composition of 24. example 125 to 132 of table
The performance data of 25. example 126 to 133 of table
Claims (18)
1. a kind of composition, the composition includes the aqueous dispersion of the compound without unreacted isocyanate groups
Body, the compound are prepared by method comprising the following steps：
(i) make (a) be selected from monoisocyanates, polyisocyanates or their mixture it is at least one containing isocyanate groups
Compound is selected from formula (1a) with (b) or at least one isocyanate-reactive compound of (1b) or their mixture reacts：
Wherein each R independently is-H；-R1；
-C(O)R1；-(CH2CH2O)n(CH(CH3)CH2O)mR2；
Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；
Each n is independently 0 to 20；
Each m is independently 0 to 20；
M+n is more than 0；
Each R1It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain alkyl of at least one unsaturated bond；
Each R2It independently is-H or includes with 6 to 30 carbon and optionally the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base,
Precondition is the then R or R when the compound has formula (1a)2At least one of be-H, and at least two in R
It is a to be selected from-C (O) R1；
-(CH2CH2O)n(CH(CH3)CH2O)mR2；
Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；
Each R3It independently is-H；-R1；-C(O)R1；
-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；
Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；
Each R4It independently is-H, includes with 6 to 30 carbon and optionally the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base,
Or combination thereof；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；
Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；
Each n ' is independently 0 to 20；
Each m ' is independently 0 to 20；
M '+n ' is more than 0；
Precondition be when the compound be formula (Ib) when, then the compound it is monosubstituted by alkyl, two substitution or three substitution,
And at least one R2、R3Or R4For-H.
2. the compound at least 50% of composition according to claim 1, wherein formula (1a) and (1b) derive for biology base
's.
3. composition according to claim 1, wherein the polyisocyanates is selected from hexamethylene diisocyanate homopolymerization
Object, 3- isocyanatomethyls -3,4,4- trimethylcyclohexylisocyanates, double-(4- isocyanatocyclohexyls) methane with
And the diisocyanate trimer of formula (IIa), (IIb), (IIc) and (IId)：
4. composition according to claim 1, wherein step (i) further include that (c) is made to be selected from water, at least one formula (IIIa)
Organic compound
R5-X (IIIa)、
The organic compound of at least one formula (IIIb)
R15-(OCH2CH(OR16)CH2)Z-OR17 (IIIb)、
Or at least one second compound reaction of their mixture；Wherein
R5Selected from-the C for optionally including at least one unsaturated group1To C30The C of linear chain or branched chain alkyl, hydroxy-functional1Extremely
C30The linear chain or branched chain C of linear chain or branched chain alkyl, hydroxy-functional1To C30Polyethers, hydroxy-functional linear chain or branched chain polyester,
The C of hydroxy-functional or amine-functionalized linear chain or branched chain organosiloxane, thiol-functional1To C30Linear chain or branched chain alkyl,
Amine-functionalized C1To C30Linear chain or branched chain alkyl,
Wherein
R7、R8And R9It is each independently-H ,-C1To C6Alkyl or combination thereof；
R10For the bivalent hydrocarbon radical of 1 to 20 carbon；
X is selected from-OH ,-C (O) OH ,-SH ,-NH (R12)、-O-(CH2CH2O)s(CH(CH3)CH2O)t-H
Or-[C (O)]-O- (CH2CH2O)s(CH(CH3)CH2O)tThe isocyanate-reactive group of-H；
R12For-H or unit price C1 to C6 alkyl；
R15、R16And R17It is each independently-H；-R18；-C(O)R18,
Precondition is at least one R15、R16Or R17For-H；
R18It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain alkyl of at least one unsaturated bond；
Z is 1 to 15；
Y is-C1；
The integer that s is 0 to 50；
The integer that t is 0 to 50；
S+t is more than 0.
5. composition according to claim 4, wherein the second compound (c) has formula (IIIa), and X is-O-
(CH2CH2O)s(CH(CH3)CH2O)t- H or-[C (O)]-O- (CH2CH2O)s(CH(CH3)CH2O)t-H。
6. composition according to claim 4, wherein the second compound (c) has formula (IIIb).
7. composition according to claim 1, wherein (b) being at least one compound selected from formula (Ia)：
Wherein R independently is-H；-R1；Or-C (O) R1。
8. composition according to claim 1, wherein (b) being at least one compound selected from formula (Ia)：
Wherein R independently is-H；-(CH2CH2O)n(CH(CH3)CH2O)mR2；Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1。
9. composition according to claim 1, wherein (b) being at least one compound selected from formula (Ib)：
10. composition according to claim 1, wherein the polyisocyanates is diisocyanate.
11. a kind of method preparing the aqueous dispersion without unreacted isocyanate groups, the method includes：
(i) make (a) be selected from monoisocyanates, polyisocyanates or their mixture it is at least one containing isocyanate groups
Compound is selected from formula (Ia) with (b) or at least one isocyanate-reactive compound of (Ib) or their mixture reacts：
Wherein each R independently is-H；-R1；-C(O)R1；
-(CH2CH2O)n(CH(CH3)CH2O)mR2；
Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；
Each n is independently 0 to 20；
Each m is independently 0 to 20；
M+n is more than 0；
Each R1It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain alkyl of at least one unsaturated bond；
Each R2It independently is-H or includes with 6 to 30 carbon and optionally the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base；
Precondition is when the compound has formula (1a), then at least one of R or R2 are-H, and in R at least
Two are selected from-C (O) R1；
-(CH2CH2O)n(CH(CH3)CH2O)mR2；Or
-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；
Each R3It independently is-H；-R1；-C(O)R1；
-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；
Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；
Each R4It independently is-H, includes with 6 to 30 carbon and optionally the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base or combination thereof；-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；
Each n ' is independently 0 to 20；
Each m ' is independently 0 to 20；
M '+n ' is more than 0；
Precondition be when the compound be formula (1b) when, then the compound it is monosubstituted by alkyl, two substitution or three substitution,
And at least one R2、R3Or R4For-H.
12. according to the method for claim 11, wherein the polyisocyanates is diisocyanate.
13. a kind of method of processing fibrous substrate, the method includes applying aqueous dispersion, institute to the surface of the base material
It includes the compound without unreacted isocyanate groups to state aqueous dispersion, and the compound passes through following steps system
It is standby：
(i) make (a) be selected from monoisocyanates, polyisocyanates or their mixture it is at least one containing isocyanate groups
Compound is selected from formula (Ia) with (b) or at least one isocyanate-reactive compound of (Ib) or their mixture reacts：
Wherein each R independently is-H；-R1；
-C(O)R1；-(CH2CH2O)n(CH(CH3)CH2O)mR2；
Or-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；
Each n is independently 0 to 20；
Each m is independently 0 to 20；
M+n is more than 0；
Each R1It independently is with 5 to 29 carbon and optionally includes the linear chain or branched chain alkyl of at least one unsaturated bond；
Each R2It independently is-H or includes with 6 to 30 carbon and optionally the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base；
Precondition is the then R or R when the compound has formula (Ia)2At least one of be-H, and at least two in R
It is a to be selected from-C (O) R1；
-(CH2CH2O)n(CH(CH3)CH2O)mR2；Or
-(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1；
Each R3It independently is-H；-R1；-C(O)R1；
-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；
Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；
Each R4It independently is-H, includes with 6 to 30 carbon and optionally the linear chain or branched chain hydrocarbon of at least one unsaturated bond
Base or combination thereof；
-(CH2CH2O)n’(CH(CH3)CH2O)m’R2；
Or-(CH2CH2O)n’(CH(CH3)CH2O)m’C(O)R1；
Each n ' is independently 0 to 20；
Each m ' is independently 0 to 20；
M '+n ' is more than 0；
Precondition be when the compound be formula (Ib) when, then the compound it is monosubstituted by alkyl, two substitution or three substitution,
And at least one R2、R3Or R4For-H；
The compound provides water-resistance to the base material being in contact with it, and optionally provides soil release performance.
14. according to the method for claim 13, wherein the polyisocyanates is diisocyanate.
15. a kind of processed base material of method according to claim 13 or 14.
16. base material according to claim 15, the base material is fiber, yarn, fabric, spunlaced nonwoven object, paper
Material or cotton leather, cellulose, jute, sisal hemp, sea grass, polyamide, polyester, polyolefin, polyacrylonitrile or their blend.
17. base material according to claim 16, wherein the fiber is acetate fiber, acrylic fiber or coir fibre；
The polyamide is aromatic polyamides；The polyolefin is polypropylene.
18. base material according to claim 15, the base material is yarn, spunlaced nonwoven object, carpet, paper wood or cotton
Leather, cellulose, wool, silk, artificial silk, jute, sisal hemp, sea grass, polyamide, polyester, polyolefin, polyacrylonitrile or they
Blend.
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| US201361806465P | 2013-03-29 | 2013-03-29 | |
| US61/806465 | 2013-03-29 | ||
| PCT/US2014/032095 WO2014160905A1 (en) | 2013-03-29 | 2014-03-28 | Non-fluorinated urethane based coatings |
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| US (1) | US10138392B2 (en) |
| EP (2) | EP3231828A1 (en) |
| JP (1) | JP6608804B2 (en) |
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Also Published As
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| EP2978788B1 (en) | 2017-11-01 |
| TW201443153A (en) | 2014-11-16 |
| JP2016524628A (en) | 2016-08-18 |
| CN105377935A (en) | 2016-03-02 |
| KR102252767B1 (en) | 2021-05-18 |
| ES2653672T3 (en) | 2018-02-08 |
| US10138392B2 (en) | 2018-11-27 |
| EP2978788A1 (en) | 2016-02-03 |
| KR20150136111A (en) | 2015-12-04 |
| JP6608804B2 (en) | 2019-11-20 |
| TWI526497B (en) | 2016-03-21 |
| WO2014160905A1 (en) | 2014-10-02 |
| EP3231828A1 (en) | 2017-10-18 |
| US20140295724A1 (en) | 2014-10-02 |
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